Process of manufacturing barbituric acid.



UNITED STATES PATENT OFFICE.

WOLFES, OF DARMSTADT, GERMANY, ASSIGNOR TO LOUIS MERCK, EMMANUEL AUGUST.

MERCK, WILHELM MERCK, AND CARL EMMANUEL MERCK. COPARTNERS AS FIRM OF E;

I MERCK, OF DAHMSTADT, GERMANY;

PROCESS OF MANUFACTURING BARBITU'RIO. ACID Specification ofLetters-Patent.

Patented Doc. 22. mos.

' Original application filed. September 22,- 1905, Serial No. 279,689.Divided and this application filed Kay 23, IQOB. I

' I Serial No. 434,659.

v To all whom 'it may concern:

Be it known that I, O'rro WoLFEs, doctor of'philosophy, a subject of theEmperor of Germany, residing at the city of Darmstadt, in the Empire ofGermany, have invented new and useful Improvements in the Processes ofManufacturing Barlzituric Acids, of which the following is aspecification.

The present application is a divisional application from my applicationSerial No.

' 279689, filed September 22nd 1905, and

covers specifically the manufacture of barbituric acids, employingdialkyl malonitrils as starting material.

I have ascertained that if guanyl-urea is condensed with cyanderivatives of the following general formula:

condensationproducts are obtained which are robably mixtures of severalsuhstances for t e reason that guanyl-urea is enabled to react in twopseudomeric forms:

' NH a) mn-co-NH-c This unsymmetrical form can be condensed.

with the above-mentioned derivatives to sullilstances of the twofollowing typical form aer HNC=NH The second symmetrical form:

The substances of all these three typical forspecific exam;

from the lye and after'it has mules, when heated with a ueors acids, areeasily converted into dialky barblturlc aclds of the well known formula:

His-0o 1 Alky1 l Alkyl BIN-C0 a the reactions probably taking place inaccordance with the following formulae:

The essential characteristics of the recess thus indicated will be seenfrom the f0 owlng le: Example. uahyZ-urea and diethyl maloml- Wile-20kg. (one half molecular proportion) of dried pulverized guanylureahydrochlorid are suspended in 30 liters of alcohol and are stirred forhour with a solution of 3.5 kg. of sodium (one and one half atomicproportion) in 75 liters of absolute alcohol. Then a filtration is madefrom the sodium chloridand the solution of the free guanylurea is heatedfor 7 hours to degrees C. with 12.2'kg. (one molecular proportion) ofdiethyl malonitrile. The forms is directly heated, a er its separationbeen washed, to-

fprecipitate which gether with grees C. and thereby converted intodiethyl arbitur c Having 5 in what m acid.

now

anner described my invention. and the same is to be performed,

What I claim as new and desire to secure by Letters Patent is:

1 The barb ituric process of manufacturing diallryl acids consisting incondensing anyl-urea with dialkyl malonitrils of the r ol lowing generalform 5 by heating the mixture of the said substances Alky1 Alkyl andsaponifyingthe resulting condensation products acids, sub

by treating these products with stantially as described.

sulfuric acid of 50% to 100 (16-,

2. The process of manufacturing diethyl barhituric acid, consisting incondensing 20 anyl-urea with diethyl malonitrile' of the 0 11/ '\CN byheating the mixture of the said sult stances 25 and saponifyingtheresulting condensation product by treating this Cproduct With acids,sulistantially as describe In testimony whereof, I have hereunto set myhand in the presence. of two subscribing witnesses.

' OTTO WOLFES.

Witnesses GEORG WARNER',

WALTER HAUSING.

It is hereby certified that in Letters Patent No. 907,665, grantedDecember 22, 1908,

the Patent Oflice.

upon the application of Otto Vvol fes, of Darmstadt, Germany, for animprovement in p Processes of Manufacturing Barbitnric Acids, an errorappears in the printed speci .fication requiring correction as follows:That portion of the formula in line 71, page 1, EN-0:0 should read HN C:O; and that the said Letters Patent should be read with this correctiontherein that the same may conform to the record of the case [swan] o. o.BILLINGS,

Acting Commissioner of Patents. I

gether with grees C. and thereby converted into diethyl arbitur c Having5 in what m acid.

now

anner described my invention. and the same is to be performed,

What I claim as new and desire to secure by Letters Patent is:

1 The barb ituric process of manufacturing diallryl acids consisting incondensing anyl-urea with dialkyl malonitrils of the r ol lowing generalform 5 by heating the mixture of the said substances Alky1 Alkyl andsaponifyingthe resulting condensation products acids, sub

by treating these products with stantially as described.

sulfuric acid of 50% to 100 (16-,

2. The process of manufacturing diethyl barhituric acid, consisting incondensing 20 anyl-urea with diethyl malonitrile' of the 0 11/ '\CN byheating the mixture of the said sult stances 25 and saponifyingtheresulting condensation product by treating this Cproduct With acids,sulistantially as describe In testimony whereof, I have hereunto set myhand in the presence. of two subscribing witnesses.

' OTTO WOLFES.

Witnesses GEORG WARNER',

WALTER HAUSING.

It is hereby certified that in Letters Patent No. 907,665, grantedDecember 22, 1908,

the Patent Oflice.

upon the application of Otto Vvol fes, of Darmstadt, Germany, for animprovement in p Processes of Manufacturing Barbitnric Acids, an errorappears in the printed speci .fication requiring correction as follows:That portion of the formula in line 71, page 1, EN-0:0 should read HN C:O; and that the said Letters Patent should be read with this correctiontherein that the same may conform to the record of the case [swan] o. o.BILLINGS,

Acting Commissioner of Patents. I

Correction in Letters Patent No i fication requiring correction asfollows:

It is hereby certified that in Letters Patent No. 907,665, grantedDecember 22, 1908,

upon the application of Otto Wolfes, 0t" Darmstadt, Germany for animprovement in Processes of Manufacturin Barbituric Acids an error aears in the rinted s eoig 1 PP P D That portion of the formula in line71, page I, HNO=O should read HN-C: :"O; and that the said LettersPatent should be read with this correction therein that the same mayconform to the record of the case in the Patent Ofiiee.

Signed and sealed this 9th day of February, A. 1)., 1909.

[SEAL] C. O. BILLINGS,

Acting Commissioner of Patents.

